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The Test for Profit Motive: Allowance of Deductions under IRC § 183 Test

What factors aid the Tax Court in deciding when an activity is entered into with a “profit motive” (with allowable ordinary and necessary expenses) versus a hobby (where losses may be taken only up to the amount of profit received)? Taxpayers can deduct all ordinary and necessary expenses paid or incurred in carrying on a trade or business,[1] for the production or collection of income,[2] or for the management, conservation, or maintenance of property held

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Income Tax Issues
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Grantor Trusts – Part IV of IV – Retained Powers and Non-Grantor Owners

In Part I of this series on Grantor Trusts, we look at the nature of trusts in general.  In Part II, we shift to a look at grantor trusts, and a few definitional rules.  In Part III and Part IV, we take a deep dive into the interests that a grantor may retain that will cause a trust to be treated as a grantor trust as well as instances in which a person other than

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Income Tax Issues
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Grantor Trusts – Part III of IV – Reversionary Interests and Powers to Control Beneficial Enjoyment

In Part I of this series on Grantor Trusts, we look at the nature of trusts in general.  In Part II, we shift to a look at grantor trusts, and a few definitional rules.  In Part III and Part IV, we take a deep dive into the interests that a grantor may retain that will cause a trust to be treated as a grantor trust as well as instances in which a person other than

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Income Tax Issues
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Grantor Trusts – Part II of IV – Introduction to Grantor Trusts

In Part I of this series on Grantor Trusts, we look at the nature of trusts in general.  In Part II, we shift to a look at grantor trusts, and a few definitional rules.  In Part III and Part IV, we take a deep dive into the interests that a grantor may retain that will cause a trust to be treated as a grantor trust as well as instances in which a person other than

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Income Tax Issues
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Grantor Trusts – Part I of IV – Introduction to Trusts and Taxes

When I told my boss that I was going to write an article on grantor trusts, he responded (without hesitation sensitivity, or thought), “You know, a lot of people have written about grantor trusts.” He’s not wrong. Not helpful—but not wrong Search Google, and you will find numerous websites with cursory discussions on grantor trusts.  Look a little deeper, and you may even find some of the very good scholarly articles that I drew from

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Income Tax Issues
Tax Articles

Understanding the Doctrine of Constructive Receipt

Uncle Bill Sells the Buick Your dear Uncle Bill calls you all in a tizzy asking for some (free) legal advice from his “favorite” nephew. You want to remind him that you are (a) the only lawyer in the family, and (b) the only one of his nephews who not currently in the hoosegow, but you think better of it and indulge him. Bill and Aunt Ethel, who apparently are back together after the Thanksgiving

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Income Tax Issues
Tax Articles

The Deductibility of Criminal Restitution & The Claim of Right Doctrine

You have made it a habit to screen your calls, even since your mother gave Uncle Bill your direct line at work. Sure enough, 5:59 PM rolls around, and you have one foot physically out of your office door when your phone rings. Mother of all that is good and holy… As you put your briefcase down in the doorway and slowly amble back to your desk, you are at once relieved that it is

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McCrory v. Commissioner (T.C. Memo. 2021-116)

On October 4, 2021, the Tax Court issued a Memorandum Opinion in the case of McCrory v. Commissioner (T.C. Memo. 2021-116). The primary issue presented in McCrory was whether the IRS Whistleblower Office’s rejections of the petitioner’s claims were unsupported by the administrative record and were arbitrary, capricious, an abuse

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Gregory v. Commissioner (T.C. Memo. 2021-115)

On September 29, 2021, the Tax Court issued a Memorandum Opinion in the case of Gregory v. Commissioner (T.C. Memo. 2021-115). The primary issue presented in Gregory was whether the claimed deductions permitted under IRC § 183(b) for activities not engaged in for profit are not subject to the 2%

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A Primer on Employment Tax Withholding

When the IRS is involved, monetary transactions are never as simple as they appear on the surface. The late, great comedian Mitch Hedberg once told a story about being given a receipt after buying a doughnut. I bought a doughnut, and they gave me a receipt for the doughnut. I

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Clark v. Commissioner (T.C. Memo. 2021-114)

On September 28, 2021, the Tax Court issued a Memorandum Opinion in the case of Clark v. Commissioner (T.C. Memo. 2021-114). The primary issue presented in Clark was whether the petitioner fraudulently underreported his income. Held:  Oh, dear God.  The fraud! The Tax Court’s Summary of the Issue in Clark

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Whistleblower 14377-16W v. Commissioner (T.C. Memo. 2021-113)

On September 27, 2021, the Tax Court issued a Memorandum Opinion in the case of Whistleblower 14377-16W v. Commissioner (T.C. Memo. 2021-113). The primary issues presented in Whistleblower 14377-16W were whether the whistleblower could proceed anonymously, and whether the WBO abused its discretion in denying the whistleblower-petitioner an award. Held:

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Brown v. Commissioner (T.C. Memo. 2021-112)

On September 23, 2021, the Tax Court issued a Memorandum Opinion in the case of Brown v. Commissioner (T.C. Memo. 2021-112). The sole issue presented in Brown was whether the Tax Court has jurisdiction to order the refund of a TIPRA payment. What is a TIPRA Payment? The Tax Increase

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